10 Iconic Style Upgrades

10 Iconic Wardrobe Staples Every Man Should Own

The art of permanent style — i.e. the kind that never goes out of fashion — lies in mastering essential items of clothing that look good in any place and time, wardrobe staples that will see you through multiple decades, career changes, wives and girlfriends, and various climates. With these 10 items you will be ready for any season or situation, and always look like a man who knows what’s important in life.

For each item we present the iconic version, of which most men with taste will have acquired at least a representative sample at some point, as well as the perfect upgrade, for those ready to advance to another level, or who want to go all out from the start. You will do very well with the icons, and we’d recommend starting with those. Upgrading is often, but not always, a matter of cost; you can expect to pay more for refinement in most cases, but not all.

And here’s a pro tip: for the best outfit of all time, wear all of them at once.

The Upgrade: Battenwear Cloudburster

Battenwear

Designed by Shinya Hasegawa in New York, Battenwear shows once again that the Japanese do classic Americana better than we can. Every detail is perfect on this all-season parka.$422.00 at PortlandDryGoods.com

Diving Watch -- The Icon: Rolex Submariner

The Upgrade: Panerai Luminor 1950

Panerai

The Luminor was developed for the Italian Navy’s elite commando units who proved devastatingly effective in World War II, and the 1950 version retains the looks of the original. Simultaneously says “well off” and “badass.”$9,100.00 at Panerai.com

The Upgrade: Helly Hansen Signal Lo

Helly Hansen

The stripe on these nautical inspired kicks from the storied Norwegian brand is a clean, classic and subtly racy touch that also lets people know you’re too smart to pay $300 for a pair of sneakers.$55.00 at HellyHansen.com

Button-Down Shirt -- The Icon: Brooks Brothers Oxford

The Upgrade: Thom Browne Grosgrain Oxford

Thom Browne

Thom Browne revolutionized menswear with his high-water suits but what he does best is twist the knob on classic wardrobe staples, like the bit of grosgrain ribbon on the placket of a perfect oxford cloth shirt.$375.00 at ThomBrowne.com

Field Bag -- The Icon: Filson Original Briefcase

Filson

Seattle’s Filson has long been the go-to for men who don’t need their briefcase to proclaim that they’re lawyers or bankers. Indestructible and stylish, they also work extremely well for weekend pursuits.$265.00 at Filson.com

Cashmere Sweater -- The Icon: J. Crew Italian Cashmere Crewneck

J. Crew

Get over the idea that cashmere is for special occasions: the best way to wear it is as you would your favorite sweatshirt — which is why your first purchase shouldn’t be too precious.$181.40 at JCrew.com